JPS62126186A - Production of isoflavone derivative - Google Patents
Production of isoflavone derivativeInfo
- Publication number
- JPS62126186A JPS62126186A JP26612585A JP26612585A JPS62126186A JP S62126186 A JPS62126186 A JP S62126186A JP 26612585 A JP26612585 A JP 26612585A JP 26612585 A JP26612585 A JP 26612585A JP S62126186 A JPS62126186 A JP S62126186A
- Authority
- JP
- Japan
- Prior art keywords
- solvent
- organic solvent
- resin
- water
- isoflavone
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Landscapes
- Saccharide Compounds (AREA)
- Pyrane Compounds (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、簡便かつ安価な、イソフラボン誘導体の製造
方法に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a simple and inexpensive method for producing isoflavone derivatives.
［従来の技術および問題点］
マメ科（Ｌｅｇｕｍｔｎｏｓａｅ）の植物であるダイズ
の種子、大豆は貴重な植物蛋白源として古くより栽培さ
れており、種々の食品の原料となっている。[Prior Art and Problems] Soybean seeds, which are plants belonging to the Fabaceae family, have been cultivated since ancient times as a valuable source of vegetable protein, and are used as raw materials for various foods.
この大豆には、蛋白質、糖質、ビタミン類の他に、下記
式
で表されるダイズイン、グリシチン、ゲニスチン、ダイ
ゼイン、ゲニステイン等のイソフラボン誘導体が含まれ
ており、ダイゼインのマウス摘出小腸におけるパパベリ
ン様鎮痙作用［薬学雑誌。In addition to proteins, carbohydrates, and vitamins, this soybean contains isoflavone derivatives such as daidzein, glycitin, genistin, daidzein, and genistein expressed by the following formula. Effect [Pharmaceutical journal.
９７、［０３（１９７７）コをはじめとして多くの薬理
作用が知られている。従って、今後これらのイソフラボ
ン誘導体を医薬品として提供する場合、いかに安価に、
かつ大量にイソフラボン誘導体を得るかが重要な因子と
なる。97, [03 (1977)) Many pharmacological actions are known, including those of Therefore, if we are to provide these isoflavone derivatives as pharmaceuticals in the future, we will need to find out how cheaply and
An important factor is whether a large amount of isoflavone derivatives can be obtained.
従来、イソフラボン誘導体を得るには、大豆の有機溶媒
または、含水有機溶媒による抽出液をアルミナ、ンリカ
ゲル等を吸着剤とするカラムクロマトグラフィーで精製
する方法がとられていた。Conventionally, isoflavone derivatives have been obtained by purifying a soybean extract with an organic solvent or a water-containing organic solvent by column chromatography using alumina, phosphoric acid gel, or the like as an adsorbent.
しかし、これらの方法を工業的大量精製に適用する場合
、吸着剤への負荷量が顕著に多くなることや、規模拡大
のために操作が煩雑になる等の不都合が生じるため、得
られるイソフラボン誘導体は少量でしかも高価なものに
なる。また、イソフラボン誘導体の工業的な精製はほと
んど行なわれていない。However, when these methods are applied to industrial large-scale purification, there are disadvantages such as a significant increase in the amount of loading on the adsorbent and complicated operations due to scale expansion, so it is difficult to obtain the isoflavone derivatives obtained. is small quantity and expensive. Furthermore, industrial purification of isoflavone derivatives has hardly been carried out.
［問題点を解決するための手段］
本発明者等は、安価に、かつ大量にイソフラボン誘導体
を得るための方法について鋭意検討した結果、大豆の抽
出液をそのままもしくは溶媒を留去して合成吸着樹脂に
接触させて、イソフラボン誘導体を吸着せしめ、次いで
有機溶媒または有機溶媒と水との混合溶媒を用いて該合
成吸着樹脂から溶出させることにより安価に、かつ大量
にイソフラボン誘導体が得られることを見出し、本発明
を完成さけた。[Means for Solving the Problems] As a result of intensive research into methods for obtaining isoflavone derivatives at low cost and in large quantities, the present inventors conducted synthetic adsorption using the soybean extract as it was or by distilling off the solvent. We have discovered that isoflavone derivatives can be obtained inexpensively and in large quantities by contacting them with a resin to adsorb them, and then eluting them from the synthetic adsorption resin using an organic solvent or a mixed solvent of an organic solvent and water. , completed the invention.
以下に本発明の詳細な説明する。The present invention will be explained in detail below.
大豆の抽出液を得る際に、抽出に用いられる大豆は、Ｇ
ｌｙｃｉｎｅ ｍａｙ、 Ｍｅｒｒｉｌｌの種子を用い
ることができる。抽出溶媒は水、有機溶媒または水と有
機溶媒との混合溶媒が挙げられ、室温から抽出溶媒の沸
点までの温度範囲内で抽出する。When obtaining a soybean extract, the soybeans used for extraction are G.
Lycine may, Merrill seeds can be used. Examples of the extraction solvent include water, an organic solvent, or a mixed solvent of water and an organic solvent, and extraction is performed within a temperature range from room temperature to the boiling point of the extraction solvent.
また、現在、味噌の製造には、全国で年間約１８万トン
の大豆が消費されており、その水煮液のほとんどは廃液
として捨てられているが、本発明で言うところの大豆の
抽出液は、このような廃液をも包含する。従って、従来
はとんど利用されていなかった味噌製造時の大豆の抽出
液を利用すれば、より安価にイソフラボン誘導体を得る
ことができる。Currently, approximately 180,000 tons of soybeans are consumed annually nationwide in the production of miso, and most of the boiled liquid is discarded as waste liquid. also includes such waste liquid. Therefore, isoflavone derivatives can be obtained at a lower cost by using the soybean extract used in the production of miso, which has not been used in the past.
次に、前記抽出液をそのままらしくは溶媒を留去して合
成吸着樹脂に接触させて、イソフラボン誘導体を吸着せ
しめる。抽出液に酸性度、塩基性塵の違いがある場合は
、イソフラボン誘導体の合成吸着樹脂への吸着率を向上
させるために適宜、適当な酸性化剤やアルカリ性化剤を
添加してｐ１１３．５〜ｐＨ５，ｏ程度の条件に保つの
が望ましく、この際の酸性化剤としては酢酸、塩酸等が
挙げられ、アルカリ性化剤としては炭酸水素ナトリウム
、水酸化ナトリウム等が挙げられる。Next, the extract is brought into contact with a synthetic adsorption resin after the solvent is distilled off and the isoflavone derivatives are adsorbed. If the extract has a difference in acidity and basic dust, add an appropriate acidifying agent or alkalinizing agent as appropriate to improve the adsorption rate of isoflavone derivatives to the synthetic adsorption resin. It is desirable to keep the pH at about 5.0, and examples of acidifying agents in this case include acetic acid, hydrochloric acid, etc., and examples of alkalinizing agents include sodium hydrogen carbonate, sodium hydroxide, etc.
また、前記抽出時に抽出溶媒として水性溶媒を使用して
いる場合は、イソフラボン誘導体の合成吸着樹脂への吸
着率を向上させるために、抽出液から使用した水性溶媒
を留去しておくことが望ましい。In addition, if an aqueous solvent is used as the extraction solvent during the extraction, it is desirable to distill off the used aqueous solvent from the extract in order to improve the adsorption rate of isoflavone derivatives to the synthetic adsorption resin. .
合成吸着樹脂の具体例としては、「ダイヤイオン）［Ｐ
樹脂」（三菱化成工業株式会社製）、「アンバーライト
ＸＡＤ樹脂」（ロームアンドハース株式会社製）、「デ
ュオライトＳ樹脂」（ダイヤモンドジャムロック社製）
等が挙げられる。A specific example of a synthetic adsorption resin is “Diaion” [P
"Resin" (manufactured by Mitsubishi Chemical Industries, Ltd.), "Amberlite XAD resin" (manufactured by Rohm and Haas Co., Ltd.), "Duolite S resin" (manufactured by Diamond Jamrock Co., Ltd.)
etc.
前記抽出液と合成吸着樹脂との接触は、バッチ法または
カラム法のいずれの方法を使用してらよい。バッチ法の
場合は、適当な容器に合成吸着樹脂を入れ、適宜撹拌す
る等、一般的な手法により行うことができる。カラム法
の場合は、通常行われる手法により達成でき、溶出速度
は、カラムの大きさ、使用する溶出溶媒等の種々の条件
を考慮して、適宜選択することができる。上記、バッチ
法お上びカラム法ともに物理吸着であるため、温度とし
ては室温程度が望ましい。The extract and the synthetic adsorption resin may be brought into contact using either a batch method or a column method. In the case of a batch method, the synthetic adsorption resin can be placed in a suitable container and stirred as appropriate, or by other common methods. In the case of a column method, this can be achieved by a commonly used method, and the elution rate can be appropriately selected in consideration of various conditions such as the size of the column and the elution solvent used. Since both the batch method and the column method described above involve physical adsorption, the temperature is preferably about room temperature.
次に、合成吸着樹脂に吸着したイソフラボン誘導体を有
機溶媒または有機溶媒と水との混合溶媒を用いて溶出さ
せる。この場合、バッチ法、カラム法のいずれを使用し
ても良く、溶出に用いる溶媒としては、有機溶媒または
有機溶媒と水との混合溶媒を用い得る。溶出溶媒の種類
、濃度、量はカラム法で行うかバッチ法で行うか、また
、用いる合成吸着樹脂の種類および量等の種々の条件を
考慮して適宜選択する。Next, the isoflavone derivative adsorbed on the synthetic adsorption resin is eluted using an organic solvent or a mixed solvent of an organic solvent and water. In this case, either a batch method or a column method may be used, and the solvent used for elution may be an organic solvent or a mixed solvent of an organic solvent and water. The type, concentration, and amount of the elution solvent are appropriately selected in consideration of various conditions such as whether the elution is performed by a column method or a batch method, and the type and amount of the synthetic adsorption resin used.
有機溶媒の具体例としては、メタノール、エタノール、
イソプロパツール、アセトン等が挙げられるが、好まし
くはアルコール類、さらに好ましくはエタノール等が挙
げられる。Specific examples of organic solvents include methanol, ethanol,
Examples include isopropanol and acetone, preferably alcohols, and more preferably ethanol.
バッチ法により得られた溶出液、またはカラム法により
得られた溶出液に複数の成分が含まれている場合には、
通常用いられる分離精製の手法（例えば、向流分配、再
結晶、カラムクロマトグラフィー等）により、精製し、
単離することができる。If the eluate obtained by the batch method or the eluate obtained by the column method contains multiple components,
Purified by commonly used separation and purification techniques (e.g. countercurrent distribution, recrystallization, column chromatography, etc.),
Can be isolated.
本発明のイソフラボン誘導体の製造方法で使用した合成
吸着樹脂は、適当な打機溶媒（例えば、アルコール系、
アセトン系有機溶媒等）または、アルカリ剤（例えば、
水酸化ナトリウム、水酸化カリウム等）により洗浄再生
することにより、繰り返し使用が可能であり、非常に経
済的である。The synthetic adsorption resin used in the method for producing isoflavone derivatives of the present invention is prepared using a suitable solvent (e.g., alcohol-based,
acetone-based organic solvents, etc.) or alkaline agents (e.g.
By washing and regenerating with sodium hydroxide, potassium hydroxide, etc., it can be used repeatedly and is very economical.
［実施例］
次に実施例を示して本発明を更に詳しく説明するが、本
発明はこれにより何ら制限されるものではない。[Examples] Next, the present invention will be explained in more detail with reference to Examples, but the present invention is not limited thereto.
実施例１
味噌製造時に得られる大豆煮汁３５Ｌを酢酸でｐｌ＋４
．０に調整した後、綿栓でＩ過し、シ戸液を得た。次に
、６００Δのメタノールと６００７ｄの水で洗／ＩＰＬ
、活性化させたスヂレンージビニルベンゼン重合樹脂（
三菱化成工業株式会社製、ダイヤイオンＬＩＰ−２０）
５００Ｊを充填した樹脂塔に、前記の５戸液を添加し、
樹脂塔内を５０ｍｆ１７ｍＨＨで通過させ、次いで６０
０燻の水、さらに２０％メタノール水溶液を加えて洗浄
を行った。洗浄後、樹脂塔に１．８文のエタノールを溶
出速度３０Ｊ ／ ｍ ｉ ｎで通過させ、ダイズイン
、グリシチン、ゲニスチン、ダイゼイン、ゲニステイン
を含有する溶液を得た。Example 1 35L of soybean broth obtained during miso production was diluted with acetic acid to pl+4
．． After adjusting to 0, it was filtered through a cotton plug to obtain Shito's liquid. Next, wash with 600Δ methanol and 6007d water/IPL
, activated styrene-divinylbenzene polymer resin (
Diaion LIP-20, manufactured by Mitsubishi Chemical Industries, Ltd.)
Add the above-mentioned 5-house liquid to a resin tower filled with 500 J,
Pass through the resin column at 50mf17mHH, then 60mf
Washing was performed by adding 0% smoked water and a 20% aqueous methanol solution. After washing, 1.8 grams of ethanol was passed through the resin tower at an elution rate of 30 J/min to obtain a solution containing daidzein, glycitin, genistein, daidzein, and genistein.
実施例２
市販の脱脂大豆２０ｇに８０％エタノール水溶液を加え
て、水浴上で４時間還流し、冷却後３戸紙で？過して得
られた抽出液５０蔵に、水１５０ｄを加え、酢酸でｐＨ
４，ｏに調整した。この液を、１００−のメタノールと
１００７ｄの水で洗浄活性化させたスチレン−ジビニル
ベンゼン重合樹脂（三菱化成工業株式会社製、ダイヤイ
オンＨＰ−２０）２０−を充填した樹脂塔に添加し、樹
脂塔内をＩｍｆＪ／ｍｉｎで通過させ、次いで、１００
−のエタノールを溶出速度５ｍｆｌ／ｍｉｎでａ過させ
、ダイズイン、グリシチン、ゲニスチン、ダイゼイン、
ゲニステインを含有する溶液を得た。Example 2 An 80% aqueous ethanol solution was added to 20 g of commercially available defatted soybeans, refluxed on a water bath for 4 hours, cooled, and washed with paper for 3 hours. 150 d of water was added to 50 ml of the extract obtained by filtration, and the pH was adjusted with acetic acid.
Adjusted to 4.o. This liquid was added to a resin column filled with 20-20% of styrene-divinylbenzene polymer resin (Diaion HP-20, manufactured by Mitsubishi Chemical Corporation) which had been washed and activated with 100% methanol and 1007% water. Passed through the column at ImfJ/min, then 100
- ethanol at an elution rate of 5 mfl/min, daidzein, glycitin, genistin, daidzein,
A solution containing genistein was obtained.
実施例３
大豆煮汁５００Ｉｎｆ！を酢酸でｐＨ４，０に調整した
溶液に、４００−のメタノールと４００−の水で活性化
させたスチレン−ジビニルベンゼン重合樹脂（三菱化成
工業株式会社製、ダイヤイオンＨＰ −２０）２０ＱＪ
ｒｆ！を添加し、時々撹拌しながら室温で２時間放置し
た。この溶液を柄出ロートでシ濾過して、その残渣をカ
ラムに移し、４００−の水を加えて洗浄を行った後、カ
ラムに７０％メタノール水溶液２又を溶出速度５０Ｊ／
ｍｉｎで通過させ褐色のプエラリン、ダイゼイン含有溶
液を、次に、メタノール２．５又で褐色のダイゼイン含
有溶液を得た。Example 3 Soybean broth 500Inf! Styrene-divinylbenzene polymer resin (manufactured by Mitsubishi Chemical Corporation, Diaion HP-20) 20QJ activated with 400-methanol and 400-m water in a solution adjusted to pH 4.0 with acetic acid.
rf! was added and left at room temperature for 2 hours with occasional stirring. This solution was filtered through a patterned funnel, the residue was transferred to a column, and after washing by adding 400 ml of water, a 70% methanol aqueous solution was added to the column at an elution rate of 50 J/2.
A brown puerarin and daidzein-containing solution was obtained by passing through the solution at 2.5 min.
Claims (1)
着樹脂に接触させて、イソフラボン誘導体を吸着せしめ
、次いで有機溶媒または有機溶媒と水との混合溶媒を用
いて該合成樹脂から溶出させてイソフラボン誘導体を得
ることを特徴とするイソフラボン誘導体の製造方法。The soybean extract is brought into contact with a synthetic adsorption resin, either as it is or after the solvent is distilled off, to adsorb isoflavone derivatives.Then, the isoflavone derivatives are eluted from the synthetic resin using an organic solvent or a mixed solvent of an organic solvent and water. A method for producing an isoflavone derivative, the method comprising obtaining a derivative.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26612585A JPS62126186A (en) | 1985-11-28 | 1985-11-28 | Production of isoflavone derivative |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP26612585A JPS62126186A (en) | 1985-11-28 | 1985-11-28 | Production of isoflavone derivative |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS62126186A true JPS62126186A (en) | 1987-06-08 |
| JPH0421670B2 JPH0421670B2 (en) | 1992-04-13 |
Family
ID=17426672
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP26612585A Granted JPS62126186A (en) | 1985-11-28 | 1985-11-28 | Production of isoflavone derivative |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62126186A (en) |
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| US6083553A (en) * | 1998-06-05 | 2000-07-04 | Protein Technologies International, Inc. | Recovery of isoflavones from soy molasses |
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| US6146668A (en) * | 1997-04-28 | 2000-11-14 | Novogen, Inc. | Preparation of isoflavones from legumes |
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| KR100347668B1 (en) * | 2000-03-24 | 2002-08-07 | 주식회사 유젠바이오 | Improved method for extration of isoflavone |
| US6444239B2 (en) | 2000-01-28 | 2002-09-03 | Kikkoman Corporation | Process for producing isoflavone aglycone-containing composition |
| JP2002308868A (en) * | 2001-04-12 | 2002-10-23 | Morita Kk | Production method for isoflavone compound having orthodihydroxy structure |
| US6479054B1 (en) | 1998-09-21 | 2002-11-12 | Showa Sangyo Co., Ltd. | Process for obtaining genistin-rich isoflavone composition |
| WO2003000674A1 (en) * | 2001-06-21 | 2003-01-03 | Fuji Oil Company,Limited | Process for producing soluble isoflavone-containing composition |
| US6544566B1 (en) | 1999-04-23 | 2003-04-08 | Protein Technologies International, Inc. | Composition containing plant sterol, soy protein and isoflavone for reducing LDL cholesterol |
| US6599536B1 (en) | 1998-03-26 | 2003-07-29 | Novogen Research Pty Ltd | Therapy of estrogen-associated disorders |
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| US6703051B1 (en) | 1998-10-13 | 2004-03-09 | Solae, Llc | Process for separating and recovering protein and isoflavones from a plant material |
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| US7713940B2 (en) | 2003-05-20 | 2010-05-11 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Water-soluble isoflavone composition, process for producing the same, and use thereof |
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| CN102206209A (en) * | 2011-04-12 | 2011-10-05 | 聊城大学 | Method for extracting and separating soybean isoflavone monomer compounds from soybeans |
| CN103788156A (en) * | 2014-02-24 | 2014-05-14 | 聊城大学 | Method for separating and purifying soy isoflavone monomer compounds |
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-
1985
- 1985-11-28 JP JP26612585A patent/JPS62126186A/en active Granted
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| JPS59187746A (en) * | 1983-04-11 | 1984-10-24 | Hayashibara Biochem Lab Inc | Beverage and its preparation |
Cited By (40)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0426998A2 (en) * | 1989-11-10 | 1991-05-15 | Societe Des Produits Nestle S.A. | Process for the preparation of isoflavanones |
| US6987098B2 (en) | 1992-05-19 | 2006-01-17 | Novogen Research Pty. Ltd. | Health supplement |
| JPH07506822A (en) * | 1992-05-19 | 1995-07-27 | ノボゲン リサーチ ピーティーワイ リミッテッド | Health supplements containing phytoestrogens, analogs or their metabolites |
| US6642212B1 (en) | 1992-05-19 | 2003-11-04 | Novogen Research Pty. Ltd. | Health supplements containing phyto-oestrogens, analogues or metabolites thereof |
| US6562380B1 (en) | 1992-05-19 | 2003-05-13 | Novogen Research Pty Limited | Methods for treating or reducing prediposition to breast cancer, pre-menstrual syndrome or symptoms associated with menopause by administration of phyto-estrogen |
| USRE40792E1 (en) | 1992-05-19 | 2009-06-23 | Novogen Research Pty Ltd | Health supplements containing phyto-oestrogens, analogues or metabolites thereof |
| US6706292B2 (en) | 1996-06-11 | 2004-03-16 | Solae, Llc | Recovery of isoflavones from soy molasses |
| US6323018B1 (en) | 1996-06-11 | 2001-11-27 | Protein Technologies Int'l Lnc. | Recovery of isoflavones from soy molasses |
| US6680381B1 (en) | 1996-06-11 | 2004-01-20 | Solae, Llc | Recovery of isoflavones from soy molasses |
| US6495141B2 (en) | 1996-06-11 | 2002-12-17 | Protein Technologies International, Inc. | Recovery of isoflavones from soy molasses |
| US6664382B2 (en) | 1996-06-11 | 2003-12-16 | Solae, Llc | Recovery of isoflavones from soy molasses |
| US5990291A (en) * | 1996-06-11 | 1999-11-23 | Protein Technologies International, Inc. | Recovery of isoflavones from soy molasses |
| US5919921A (en) * | 1996-06-11 | 1999-07-06 | Protein Technologies International, Inc. | Recovery of isoflavones from soy molasses |
| US7202273B2 (en) | 1996-08-30 | 2007-04-10 | Novogen Research Pty Ltd | Therapeutic methods and compositions involving isoflavones |
| US6649648B1 (en) | 1996-08-30 | 2003-11-18 | Novogen Research Pty Limited | Therapeutic methods and compositions involving isoflavones |
| US6146668A (en) * | 1997-04-28 | 2000-11-14 | Novogen, Inc. | Preparation of isoflavones from legumes |
| US6340703B1 (en) | 1997-05-01 | 2002-01-22 | Novogen, Inc. | Treatment or prevention of osteoporosis |
| US6004558A (en) * | 1998-02-25 | 1999-12-21 | Novogen, Inc. | Methods for treating cancer with legume plant extracts |
| US6132795A (en) * | 1998-03-15 | 2000-10-17 | Protein Technologies International, Inc. | Vegetable protein composition containing an isoflavone depleted vegetable protein material with an isoflavone containing material |
| US6599536B1 (en) | 1998-03-26 | 2003-07-29 | Novogen Research Pty Ltd | Therapy of estrogen-associated disorders |
| US6083553A (en) * | 1998-06-05 | 2000-07-04 | Protein Technologies International, Inc. | Recovery of isoflavones from soy molasses |
| US6479054B1 (en) | 1998-09-21 | 2002-11-12 | Showa Sangyo Co., Ltd. | Process for obtaining genistin-rich isoflavone composition |
| US6703051B1 (en) | 1998-10-13 | 2004-03-09 | Solae, Llc | Process for separating and recovering protein and isoflavones from a plant material |
| US6579534B2 (en) | 1999-04-23 | 2003-06-17 | Solae, Llc | Composition containing soy hypocotyl material and plant sterol for reducing LDL-cholesterol |
| US6572876B2 (en) | 1999-04-23 | 2003-06-03 | Solae, Llc | Administering a composition containing plant sterol, soy protein and isoflavone for reducing LDL-cholesterol |
| US6544566B1 (en) | 1999-04-23 | 2003-04-08 | Protein Technologies International, Inc. | Composition containing plant sterol, soy protein and isoflavone for reducing LDL cholesterol |
| US6669952B2 (en) | 1999-04-23 | 2003-12-30 | Solae, Llc | Composition containing isoflavone material and plant sterol for reducing LDL-cholesterol |
| US7285297B1 (en) | 1999-04-23 | 2007-10-23 | Archer-Daniels-Midland Company | Method of reducing low density liproprotein cholesterol concentration |
| US7488494B2 (en) | 1999-09-06 | 2009-02-10 | Novogen Research Pty Ltd. | Compositions and therapeutic methods involving isoflavones and analogues thereof |
| US6444239B2 (en) | 2000-01-28 | 2002-09-03 | Kikkoman Corporation | Process for producing isoflavone aglycone-containing composition |
| KR100347668B1 (en) * | 2000-03-24 | 2002-08-07 | 주식회사 유젠바이오 | Improved method for extration of isoflavone |
| US7312344B2 (en) | 2001-03-08 | 2007-12-25 | Novogen Research Pty Limited | Dimeric isoflavones |
| JP2002308868A (en) * | 2001-04-12 | 2002-10-23 | Morita Kk | Production method for isoflavone compound having orthodihydroxy structure |
| WO2003000674A1 (en) * | 2001-06-21 | 2003-01-03 | Fuji Oil Company,Limited | Process for producing soluble isoflavone-containing composition |
| US7015339B2 (en) | 2001-07-24 | 2006-03-21 | Cargill, Incorporated | Process for isolating phenolic compounds |
| US7560131B2 (en) | 2002-12-24 | 2009-07-14 | Fuji Oil Company, Limited | High solubility composition with high isoflavone concentration and process of producing same |
| US7713940B2 (en) | 2003-05-20 | 2010-05-11 | Kabushiki Kaisha Hayashibara Seibutsu Kagaku Kenkyujo | Water-soluble isoflavone composition, process for producing the same, and use thereof |
| US7993684B2 (en) | 2003-09-19 | 2011-08-09 | Sunstar Inc. | Method of inhibiting alveolar bone resorption and periodontal membrane loss and composition for internal use to be used therein |
| CN102206209A (en) * | 2011-04-12 | 2011-10-05 | 聊城大学 | Method for extracting and separating soybean isoflavone monomer compounds from soybeans |
| CN103788156A (en) * | 2014-02-24 | 2014-05-14 | 聊城大学 | Method for separating and purifying soy isoflavone monomer compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0421670B2 (en) | 1992-04-13 |
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